Rhizovarins A-F, Indole-Diterpenes from the Mangrove-Derived Endophytic Fungus Mucor irregularis QEN-189

Journal of Natural Products

Volumn 79, Issue 8, 2016, Pages 2066-2074

  Gao, Shu Shan ^a,b   Li, Xiao Ming ^a   Williams, Katherine ^b   Proksch, Peter ^c   Ji, Nai Yun ^d   Wang, Bin Gui ^a  

^a INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^b UNIVERSITY OF BRISTOL   (United Kingdom)

^c HEINRICH HEINE UNIVERSITY   (Germany)

^d YANTAI INSTITUTE OF COASTAL ZONE RESEARCH   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL; ACETAL DERIVATIVE; ANTINEOPLASTIC AGENT; DITERPENE; DOXORUBICIN; HEMIKETAL; INDOLE DERIVATIVE; PAXILLINE; RHIZOVARIN A; RHIZOVARIN B; RHIZOVARIN C; RHIZOVARIN D; RHIZOVARIN E; RHIZOVARIN F; UNCLASSIFIED DRUG; HERBACEOUS AGENT;

A549 CELL LINE; ANALYTIC METHOD; ANTINEOPLASTIC ACTIVITY; ARTICLE; CALCULATION; CONTROLLED STUDY; CYTOTOXICITY; DRUG DESIGN; DRUG ISOLATION; DRUG SYNTHESIS; ENDOPHYTIC FUNGUS; FUNGAL STRAIN; FUNGUS ISOLATION; HL 60 CELL LINE; HUMAN; HUMAN CELL; IC50; MANGROVE; MOSHER METHOD; MUCOR; MUCOR IRREGULARIS; NUCLEOTIDE SEQUENCE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG SCREENING; HL-60 CELL LINE; ISOLATION AND PURIFICATION; MICROBIOLOGY; RHIZOPHORACEAE; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; CRYSTALLOGRAPHY, X-RAY; DITERPENES; DRUG SCREENING ASSAYS, ANTITUMOR; DRUGS, CHINESE HERBAL; HL-60 CELLS; HUMANS; INDOLES; MOLECULAR STRUCTURE; MUCOR; RHIZOPHORACEAE;

EID: 84984685525     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/acs.jnatprod.6b00403     Document Type: Article

References (39)

1. Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2014, 79, 629-661 10.1021/acs.jnatprod.5b01055
2. Blunt, J. W.; Copp, B. R.; Keyzers, R. A.; Munro, M. H. G.; Prinsep, M. R. Nat. Prod. Rep. 2015, 32, 116-211 10.1039/C4NP00144C
3. Meng, L. H.; Li, X. M.; Liu, Y.; Wang, B. G. Org. Lett. 2014, 16, 6052-6255 10.1021/ol503046u
4. Liu, Z.; Chen, Y.; Chen, S.; Liu, Y.; Lu, Y.; Chen, D.; Lin, Y.; Huang, X.; She, Z. Org. Lett. 2015, 18, 1406-1409 10.1021/acs.orglett.6b00336
5. Bladt, T. T.; Frisvad, J. C.; Knudsen, P. B.; Larsen, T. O. Molecules 2013, 18, 11338-11376 10.3390/molecules180911338
6. Baltz, R. H. J. Ind. Microbiol. Biotechnol. 2006, 33, 507-513 10.1007/s10295-005-0077-9
7. Zhang, P.; Mandi, A.; Li, X. M.; Du, F. Y.; Wang, J. N.; Li, X.; Kurtan, T.; Wang, B. G. Org. Lett. 2014, 16, 4834-4837 10.1021/ol502329k
8. Meng, L. H.; Du, F. Y.; Li, X. M.; Pedpradab, P.; Xu, G. M.; Wang, B. G. J. Nat. Prod. 2015, 78, 909-913 10.1021/np5007839
9. Liu, H.; Li, X. M.; Liu, Y.; Zhang, P.; Wang, J. N.; Wang, B. G. J. Nat. Prod. 2016, 79, 806-811 10.1021/acs.jnatprod.5b00893
10. Akone, S. H.; Daletos, G.; Lin, W. H.; Proksch, P. Z. Naturforsch., C: J. Biosci. 2016, 71c, 15-19 10.1515/znc-2015-0137
11. Rundberget, T. A.; Wilkins, L. Phytochemistry 2002, 61, 979-985 10.1016/S0031-9422(02)00369-2
12. Zhang, S.; Monahan, B. J.; Tkacz, J. S.; Scott, B. Appl. Environ. Microbiol. 2004, 70, 6875-6883 10.1128/AEM.70.11.6875-6883.2004
13. Laakso, J. A.; Gloer, J. B.; Wicklow, D. T.; Wowd, P. F. J. Agric. Food Chem. 1993, 41, 973-975 10.1021/jf00030a027
14. De Jesus, A. E.; Steyn, P. S.; van Heerden, F. R.; Vleggaar, R.; Wessels, P. L. J. Chem. Soc., Perkin Trans. 1 1983, 1847-1856 10.1039/P19830001847
15. De Jesus, A. E.; Steyn, P. S.; van Heerden, F. R.; Vleggaar, R.; Wessels, P. L. J. Chem. Soc., Perkin Trans. 1 1983, 1857-1861 10.1039/P19830001857
16. Smith, A. B.; Kanoh, N.; Ishiyama, H.; Minakawa, N.; Rainier, J. D.; Hartz, R. A.; Cho, Y. S.; Cui, H.; Moser, W. H. J. Am. Chem. Soc. 2003, 125, 8228-8237 10.1021/ja034842k
17. Sallam, A. A.; Ayoub, N. M.; Foudah, A. I.; Gissendanner, C. R.; Meyer, S. A.; Sayed, K. A. E. Eur. J. Med. Chem. 2013, 70, 594-606 10.1016/j.ejmech.2013.09.045
18. Wang, S.; Li, X. M.; Teuscher, F.; Li, D. L.; Diesel, A.; Ebel, R.; Proksch, P.; Wang, B. G. J. Nat. Prod. 2006, 69, 1622-1625 10.1021/np060248n
19. Blin, K.; Medema, M. H.; Kazempour, D.; Fischbach, M. A.; Breitling, R.; Takano, E.; Weber, T. Nucleic Acids Res. 2013, 41, W204-W-212 10.1093/nar/gkt449
20. Calculator Plugins were used for structure property prediction and calculation, Marvin 5.9.2, 2012, ChemAxon (http://www.chemaxon.com).
21. Li, S.; Zhou, W.; Gao, H.; Zhou, Z. Magn. Reson. Chem. 2012, 50, 106-113 10.1002/mrc.2837
22. Bringmann, G.; Bruhn, T.; Maksimenka, K.; Hemberger, Y. Eur. J. Org. Chem. 2009, 2009, 2717-2727 10.1002/ejoc.200801121
23. Bruhn, T.; Hemberger, Y.; Schaumlöffel, A.; Bringmann, G. SpecDis, Version 1.51; University of Wuerzburg: Germany, 2011.
24. Wang, B. G.; Ebel, R.; Wang, C. Y.; Wray, V.; Proksch, P. Tetrahedron Lett. 2002, 43, 5783-5787 10.1016/S0040-4039(02)01180-2
25. Belofsky, G. N.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. Tetrahedron 1995, 51, 3959-3968 10.1016/0040-4020(95)00138-X
26. Laakso, J. A.; Gloer, J. B.; Wicktow, D. T.; Dowd, P. F. J. Org. Chem. 1992, 57, 2066-2071 10.1021/jo00033a030
27. Moldes-Anaya, A.; Rundberget, T.; Uhlig, S.; Rise, F.; Wilkins, A. L. Toxicon 2011, 57, 259-265 10.1016/j.toxicon.2010.11.020
28. Itabashi, T.; Hosoe, T.; Wakana, D.; Fukushima, K.; Takizawa, K.; Yaguchi, T.; Okada, K.; Takaki, G. M.; Kawai, K. J. Nat. Med. 2009, 63, 96-99 10.1007/s11418-008-0292-6
29. Sun, H.; Gao, S. S.; Li, X. M.; Li, C. S.; Wang, B. G. Chin. J. Oceanol. Limnol. 2013, 31, 464-470 10.1007/s00343-013-2106-2
30. Yamaguchi, T.; Nozawa, K.; Hosoe, T.; Nakajima, S.; Kawai, K. I. Phytochemistry 1993, 32, 1177-1181 10.1016/S0031-9422(00)95087-8
31. Nozawa, K.; Nakajima, S.; Kawai, K. I. J. Chem. Soc., Perkin Trans. 1 1988, 2607-2610 10.1039/p19880002607
32. Nozawa, K.; Horie, Y.; Udagawa, S.; Kawai, K.; Yamazaki, M. Chem. Pharm. Bull. 1989, 37, 1387-1389 10.1248/cpb.37.1387
33. Zhang, Y. H.; Huang, S. D.; Pan, H. Q.; Bian, X. Q.; Wang, Z. Y.; Han, A. H.; Bai, J. Magn. Reson. Chem. 2014, 52, 306-309 10.1002/mrc.4065
34. Fan, Y. Q.; Wang, Y.; Liu, P. P.; Fu, P.; Zhu, T. H.; Wang, W.; Zhu, W. M. J. Nat. Prod. 2013, 76, 1328-1336 10.1021/np400304q
35. Mantle, P. G.; Weedon, C. M. Phytochemistry 1994, 36, 1209-1217 10.1016/S0031-9422(00)89639-9
36. De Jesus, A. E.; Gorst-Allman, C. P.; Steyn, P. S.; van Heerden, F. R.; Vleggaar, R.; Wessels, P. L. J. Chem. Soc., Perkin Trans. 1 1983, 1863-1868 10.1039/p19830001863
37. Liu, C.; Tagami, K.; Minami, A.; Matsumoto, T.; Frisvad, J. C.; Suzuki, H.; Ishikawa, J.; Gomi, K.; Oikawa, H. Angew. Chem., Int. Ed. 2015, 54, 5748-5752 10.1002/anie.201501072
38. Mosmann, T. J. Immunol. Methods 1983, 65, 55-63 10.1016/0022-1759(83)90303-4
39. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R. J. Natl. Cancer Inst. 1990, 82, 1107-1112 10.1093/jnci/82.13.1107